ORGN 432 |
| HIV protease specifically cleaves the imide bond between phenylalanine and proline. So the design of a molecule, mimicking the stereo electronic environment of this scissile bond may lead to potent inhibitors. While, unnatural amino acids, mainly Beta-amino acids, are known to invoke a turn structure in small peptides. Beta-amino acids have also been successfully used in creating peptidomimetics that not only have potent biological activity, but also are resistant to proteolysis. We have undertaken the synthesis of acyclic peptides based on homophenylglycine (Beta-Phg)-L-Proline that have been transformed into cyclic peptides by ring closing metathesis (RCM) reaction. These cyclizations result into the concomitant formation of unnatural linker amino acids, 6-amino hexanoic acid (Aha), 6-hydroxy hexanoic acid and Gamma-amino butanoic acid (GABA). The detailed synthesis and influence of the linker on conformational properties of such cyclic peptides will be discussed.
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Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster
Division of Organic Chemistry |
